A straightforward glycosylation method is described to regio‐ and stereoselectively introduce two α‐
l
‐fucose moieties directly to the secondary rim of β‐cyclodextrin. Using NMR and MS fragmentation studies, the nonasaccharide structure was determined, which was also visualized using molecular dynamics simulations. The reported glycosylation method proved to be robust on gram‐scale, and may be generally applied to directly glycosylate β‐cyclodextrins to make well‐defined multivalent glycoclusters.
Invited for the cover of this issue is the group of Marthe Walvoort at the University of Groningen. The image depicts a cyclodextrin ring as a dartboard, which is hit with fucose darts at specific positions to give a di‐fucosylated product. Read the full text of the article at 10.1002/chem.201806090.
A regioselective method to directly attach two fucosides to β‐cyclodextrin has been discovered. With seven positions available on the secondary rim, the major product turned out to display the 3A,3D substitution pattern. Molecular dynamics simulations of the nonasaccharide product revealed tilting and bending of the fucosylated cyclodextrin residues, suggesting some degree of flexibility in this novel glycocluster. More information can be found in the Full Paper by M. T. C. Walvoort et al. on page 6722.
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